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Stereoselective synthesis of glycosyl azides from anomeric hydroxides via protecting group manipulations. 2023

Sourav Nayak, and Somnath Yadav
Department of Chemistry & Chemical Biology, Indian Institute of Technology (ISM) Dhanbad, Dhanbad, 826004, Jharkhand, India.

Herein, we report the direct conversion of anomeric hydroxides to glycosyl azides in one step using diphenylphosphoryl azide. Protecting group manipulations on the hexose sugars have enabled the stereoselective synthesis of either the α-glycosyl azides or the β-anomeric azides in moderate to very good yields. The reaction has also been successfully used to enable the synthesis of β-2-deoxy-2-aminoglucosyl azides.

UI MeSH Term Description Entries
D006027 Glycosides Any compound that contains a constituent sugar, in which the hydroxyl group attached to the first carbon is substituted by an alcoholic, phenolic, or other group. They are named specifically for the sugar contained, such as glucoside (glucose), pentoside (pentose), fructoside (fructose), etc. Upon hydrolysis, a sugar and nonsugar component (aglycone) are formed. (From Dorland, 28th ed; From Miall's Dictionary of Chemistry, 5th ed) Glycoside
D001386 Azides Organic or inorganic compounds that contain the -N3 group. Azide
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer

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